title: Synthesis of (-)-homogalanthamine from naltrexone.
abstract: Acetylcholinesterase inhibitor (-)-homogalanthamine 3 was synthesized from μ opioid antagonist naltrexone (2) in 16% total yield. The synthesis features Grob fragmentation as a key reaction, which was especially accelerated in the presence of 15-crown-5.
authors.affiliation: School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Naoshi
authors.initials: N
authors.lastname: Yamamoto
authors.forename: Hideaki
authors.initials: H
authors.lastname: Fujii
authors.forename: Satomi
authors.initials: S
authors.lastname: Imaide
authors.forename: Shigeto
authors.initials: S
authors.lastname: Hirayama
authors.forename: Toru
authors.initials: T
authors.lastname: Nemoto
authors.forename: Junji
authors.initials: J
authors.lastname: Inokoshi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tomoda
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nagase
mesh_terms: D043844:Crown Ethers / Q000737:chemistry*; D005702:Galantamine / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009271:Naltrexone / Q000138:chemical synthesis* / Q000737:chemistry*; D009292:Narcotic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry*; D017450:Receptors, Opioid, mu / Q000037:antagonists & inhibitors* / Q000737:chemistry*
chemical_list: D043844:Crown Ethers; D009292:Narcotic Antagonists; D017450:Receptors, Opioid, mu; D005702:Galantamine; C042148:15-crown-5; D009271:Naltrexone